Would Russia Use a Nuclear Weapon If Ukraine Breaks Through the Lines?

Just a day before President Trump’s prime-time Thursday address to the nation, which is expected to focus in part on “election integrity,” Michigan Secretary of State Jocelyn Benson joins Jake Sullivan and Jon Finer to discuss the security of the 2026 midterm elections — and why she believes the election will be free, fair, and held on schedule, despite growing threats from disinformation, foreign interference, and sustained federal pressure on state election systems.

They discuss Trump’s attacks on mail voting, the SAVE Act, claims about noncitizen voting, attempts to access voter rolls, the dismantling of federal election security infrastructure, and what could happen if federal agents are sent to polling places under the banner of protecting elections.

Then, Jake and Jon turn to Russia’s war in Ukraine, taking on the roles of advisors to President Vladimir Putin in a Red Team/Blue Team exercise to debate whether Russia should escalate against NATO as Ukraine gains ground — and what risks that would pose for Europe, the U.S., and the future of the alliance.

For exclusive access to special segments, transcripts, and more, become a subscriber to the Long Game on Substack. This week, Jake and Jon broke down the strategic questions emerging from the latest developments in Iran and the Strait of Hormuz, including the unraveling ceasefire and Trump’s decision to reimpose a blockade of Iran's ports and cargo.

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